Novel 3-substituted ocotillol-type triterpenoid derivatives as antibacterial candidates

Chemical Biology and Drug Design

Volumn 84, Issue 4, 2014, Pages 489-496

  Bi, Yi ^a   Ma, Cong ^b   Zhang, Hengyuan ^c   Zhou, Zhiwen ^c   Yang, Jian ^a   Zhang, Zhenlei ^a   Meng, Qingguo ^a   Lewis, Peter J ^b   Xu, Jinyi ^c  

^a YANTAI UNIVERSITY   (China)

^b UNIVERSITY OF NEWCASTLE   (Australia)

^c CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

antibacterial activity; ocotillol type; synergistic effect; triterpenoid saponin

Indexed keywords

ANTIINFECTIVE AGENT; GINSENOSIDE; OCOTILLOL; TRITERPENE;

BACILLUS SUBTILIS; CHEMISTRY; DRUG EFFECTS; DRUG POTENTIATION; METABOLISM; MICROBIAL SENSITIVITY TEST; PANAX; STAPHYLOCOCCUS AUREUS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; DRUG SYNERGISM; GINSENOSIDES; MICROBIAL SENSITIVITY TESTS; PANAX; STAPHYLOCOCCUS AUREUS; TRITERPENES;

EID: 84900932318     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12337     Document Type: Article

References (22)

1. Arias C.A., Murray B.E., (2009) Antibiotic-resistant bugs in the 21st century-a clinical super-challenge. N Engl J Med; 360: 439-443.
2. Laidman J., (2013) Despite growing crisis, few new antibiotics are in pipeline. Medscape Medical News; April 22.
3. Hill R.A., Connolly J.D., (2012) Triterpenoids. Nat Prod Rep; 29: 780-818.
4. Augustin J.M., Kuzina V., Andersen S.B., Bak S., (2011) Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry; 72: 435-457.
5. Melzig M.F., Bader G., Loose R., (2001) Investigations of the mechanism of membrane activity of selected triterpenoidsaponins. Planta Med; 67: 43-48.
6. Li X.X., Davis B., Haridas V., Gutterman J.U., Colombini M., (2005) Proapoptotic triterpene electrophiles (avicins) form channels in membranes: cholesterol dependence. Biophys J; 88: 2577-2584.
7. Lorent J., Le Duff C.S., Quetin-Leclercq J., Mingeot-Leclercq M.P., (2013) Induction of highly curved structures in relation to membrane permeabilization and budding by the triterpenoid saponins, α-and δ-Hederin. J Biol Chem; 88: 14000-14017.
8. Ding B., Guan Q., Walsh J.P., Boswell J.S., Winter T.W., Winter E.S., Boyd S.S., Li C., Savage P.B., (2002) Correlation of the antibacterial activities of cationic peptide antibiotics and cationic steroid antibiotics. J Med Chem; 45: 663-669.
9. Tanaka N., Kinoshita T., Masukawa H., (1969) Mechanism of inhibition of protein synthesis by fusidic acid and related steroidal antibiotics. J Biochem; 65: 459-464.
10. Zhou Z., Ma C., Zhang H., Bi Y., Chen X., Tian H., Xie X., Meng Q., Lewis P.J., Xu J., (2013) Synthesis and biological evaluation of novel ocotillol-type triterpenoid derivatives as antibacterial agents. Eur J Med Chem; 68: 444-453.
11. Ma C., Yang X., Kandemir H., Mielczarek M., Johnston E.B., Griffith R., Kumar N., Lewis P.J., (2013) Inhibitors of bacterial transcription initiation complex formation. ACS Chem Biol; 8: 972-1980.
12. Seiji F., Ryoji K., Kazuhiro O., Kazuo Y., Chiu M.H., Nie R.L., Osamu T., (1995) Dammarane glycosides from aerial part of Neoalsomitra Integrifoliola. Phytochemistry; 39: 591-602.
13. B. Subtilis was used as an initial model representative of the spore-forming firmicutes that includes pathogens such as B. cereus and B. anthracis.
14. Gur'yanova E.N., Gol'dshtein I.P., Perepelkova T.I., (1976) The polarity and strength of the intermolecular hydrogen bond. Russ Chem Rev; 45: 792-806.
15. Simperler A., Watt S.W., Bonnet P.A., Jones W., Motherwell W.D.S., (2006) Correlation of melting points of inositols with hydrogen bonding patterns. Cryst Eng Comm; 8: 589-600.
16. Böhme S., Padmavathi P.V.L., Holterhues J., Ouchni F., Klarea J.P., Steinhoff H.J., (2009) Topology of the amphipathic helices of the colicin A pore-forming domain in E. Coli lipid membranes studied by pulse EPR. Phys Chem Chem Phys; 11: 6770-6777.
17. Findlay B., Zhanel G.G., Schweizer F., (2010) Cationic amphiphiles, a new generation of antimicrobials inspired by the natural antimicrobial peptide scaffold. Antimicrob Agents Chemother; 54: 4049-4058.
18. Vincent W.R., Martin C.A., Winstead P.S., Smith K.M., Gatz J., Lewis D.A., (2009) Effects of a pharmacist-to-dose computerized request on promptness of antimicrobial therapy. J Am Med Inform Assoc; 16: 47-53.
19. Wright G.L., Harper J., (1970) Fusidic acid and lincomycin therapy in staphylococcal infections in cystic fibrosis. Lancet; 7636: 9-14.
20. Delcour A.H., (2009) Outer membrane permeability and antibiotic resistance. Biochim Biophys Acta; 1794: 808-816.
21. Mortimer P.G., Piddock L.J., (1993) The accumulation of five antibacterial agents in porin-deficient mutants of Escherichia coli. J Antimicrob Chemother; 32: 195-213.
22. Chan B.C.L., Ip M., Gong H., Lui S.L., See R.H., (2013) Synergistic effects of diosmetin with erythromycin against ABC transporter over-expressed methicillin-resistant Staphylococcus aureus (MRSA) RN4220/UL5054 and inhibition of MRSA pyruvate kinase. Phytomedicine; 20: 611-614.